The invention herein described was made in the course of or under a contract thereunder with the United States Air Force Systems Command.
This invention relates to mixtures of alkyl ethers of Binor-S resulting from the alcoholysis of Binor-S in the presence of primary alcohols during the hydrogenolysis of Binor-S. More particularly, the invention relates to mixtures of hexacyclic alkyl ethers resulting from the alcoholysis of Binor-S, a C.sub.14 heptacyclic saturated hydrocarbon during hydrogenolysis of Binor-S in the presence of primary alcohols and promoting amounts of hydrogen halide or its equivalent.
It is an object of present invention to provide novel composition of alkyl ethers of hexacyclics which composition is characterized by a low freezing point, a low melting point and by favorable net volumetric heat of combustion. Said composition has utility as a high energy fuel which can be used in either jet or rocket propulsion. Jet propulsion includes a jet engine which can be used for a missile or a plane or other devices and includes the three basic types, i.e., ramjet, turbo-jet and pulse jet. The term jet generally refers to a device requiring air whereas rocket generally refers to a device containing its own oxygen.
It is an object to also provide novel compositions wherein the compositions are essentially alkyl ethers of hexacyclics.
It is also an object of present invention to provide a novel method for preparing the foregoing novel compositions.
Preparation of Binor-S is disclosed in Journal of the American Chemical Society; 88:21, Nov. 5, 1966, pages 4890-4894, title of Article ".pi. Complex Multicenter Reactions Promoted by Binuclear Catalyst Systems." "Binor-S", a New Heptacyclotetradecane via Stereospecific Dimerization of Bicycloheptadiene", by G. N. Schrauzer, B. N. Bastian and G. A. Fosselius. Binor-S is known by its chemical name of endo, cis, endoheptacyclo[5.3.1.1.sup.2,6 .1.sup.4,12 .1.sup.9,11 0.sup.3,6 .0.sup.8,10 ]tetradecane. Its melting point is about 65.degree. C. Binor-S can be depicted by the following structural formula: ##STR1## Binor-S is a C.sub.14 H.sub.16 hydrocarbon containing seven rings and a C/H atomic ratio of 0.875.
Preparation of dimers of bicycloheptadiene is disclosed in U.S. Pat. No. 3,326,993, issued June 20, 1967. The latter disclosed that a mixture of bicycloheptadiene dimers has utility as high energy fuel.
Hydrogenation of the foregoing bicycloheptadiene dimers improves its stability towards autoxidation, thereby enhancing its utility as a fuel. Such hydrogenated dimers of bicycloheptadiene, in which crystallization has been produced by maintaining at -110.degree. F. (-78.9.degree. C) are completely melted only by warming to +25.degree. F. (-3.9.degree. C). The rather high melting point of the last crystalline material of said dimer can hinder its fluid flow at low ambient temperatures.
In contrast applicant's entire product has a pour point of -75.degree. F. (-59.3.degree. C), a density of 1.0987 and a net volumetric heat of combustion of 159,600 BTU per gallon.